Diketene → HCID 13822786, compound

HRID 569170Notes

Reaction equation

HRID 569170 reaction equation
[CH3:1][N:2]([CH2:20][CH2:21][OH:22])[CH2:3]/[C:4](/[CH3:19])=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)=[CH:8][CH:7]=1.[CH2:23]=[C:24]1[O:28][C:26](=[O:27])[CH2:25]1>C(OCC)(=O)C>[C:26]([O:22][CH2:21][CH2:20][N:2]([CH3:1])[CH2:3]/[C:4](/[CH3:19])=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)=[CH:8][CH:7]=1)(=[O:27])[CH2:25][C:24]([CH3:23])=[O:28]

Participants

4

Reactant 2

HCID 12661DiketeneHCID 13822784HCID 13822784, compound

Product 1

HCID 13822786HCID 13822786, compoundYield 65.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

In 5 ml of ethyl acetate was dissolved 1.26 g of 2-[N-methyl-N-[(E)-3-[4-(pyridin-3-ylmethyl)phenyl]-2-methylallyl]amino]ethanol, and to the resulting solution was dropwise added a mixture of 0.36 ml of diketene and 1 ml of ethyl acetate under reflux over one hour, after which the resulting mixture was subjected to reaction at the same temperature for 30 minutes. Subsequently, the solvent was removed by distillation under reduced pressure, and the residue thus obtained was purified by a column chromatography [Wako Silica Gel C-200, eluant: benzene:ethyl acetate (1:1 by volume)] to obtain 1.06 g (yield 65.8%) of colorless, oily 2-[N-methyl-N-[(E)-3-[4-(pyridine-3-ylmethyl)phenyl]-2-methylallyl]amino]ethyl acetoacetate.

Workup

  1. additionto the resulting solution was dropwise added
  2. temperatureunder reflux over one hour
  3. customafter which the resulting mixture was subjected to reaction at the same temperature for 30 minutes
  4. customSubsequently, the solvent was removed by distillation under reduced pressure
  5. customthe residue thus obtained
  6. customwas purified by a column chromatography [Wako Silica Gel C-200, eluant: benzene:ethyl acetate (1:1 by volume)]

Sources & evidence

ORD record
ord-0503bbed806a47a8a114ddc00781b310
Source dataset
uspto-grants-1988_03
Patent number
US04731370

Reaction notes

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